2,9-Dimethyl-1,10-phenanthroline → 4-(6-Amino-pyridin-3-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

참여 물질

역할	이름	HCID	투입량
반응물	2,9-Dimethyl-1,10-phenanthroline	HCID 65237	—
반응물	2-Pyridinamine, 5-iodo-	HCID 88579	—
반응물	Magnesium	HCID 5462224	—
반응물	tert-Butyl 4-sulfanylpiperidine-1-carboxylate	HCID 21906090	—
반응물	Sodium t-butoxide	HCID 23676156	—
촉매	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
용매	Toluene	HCID 1140	—
생성물	4-(6-Amino-pyridin-3-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester	HCID 67427320	81.4%

반응 조건

온도	110 °C

반응 단계

Add dry toluene (6.06 mL) to a mixture of 2,9-dimethyl-1,10-phenanthroline (76.52 mg), copper(I) iodide (69.27 mg), sodium tert-butoxide (475.59 mg), 4-mercapto-piperidine-1-carboxylic acid tert-butyl ester (583.5 mg), magnesium (49.10 mg) and 2-amino-5-iodopyridine (550 mg). Bubble nitrogen into the mixture with ultrasound and stir the suspension at 110° C. in a sealed tube for 24 h. Cool and filter through celite. Wash with toluene and remove the solvent under vacuum. Add hexane/EA (1/1) and filter through a celite/silica gel pad, washing twice with hexane/EA (1/1) and then EA. Remove the solvent under vacuum. Purify by silica gel column chromatography eluting with hexane/EA (50-75%) to afford 630 mg of the title compound. MS (ES+): m/z=310 (M+H)+

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07855211B2
출처 데이터셋	uspto-grants-2010_12
ORD ID	ord-bee74f59518041d09dfddf5b94f00686
출처 메모	uspto-grants-2010_12